There was a clear difference in potency between the two oxazoline isomers

June 07, 2024

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  There was a clear difference in potency between the two oxazoline isomers

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  Design and optimization of benzimidazole-containing transient receptor potential melastatin 8 (TRPM8) antagonists

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  Table 1

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  There was a clear difference in potency between the two oxazoline isomers: oxazoline 2 was 10-fold more potent than oxazoline1  (Table 1). In addition, the highly polar imidazoline 3 showed poor activity, which may be a consequence of the protonation of the basic cyclic amidine functionality (calculated pKa ca. 9.3).16  The isoxazoline analogue (4) is comparable in potency to oxazoline 2; however, a distinguishing attribute of 4 was its greater metabolic stability in all three species. Therefore, efforts focused on the isoxazoline tether.